Mammary solid papillary carcinoma and usual duct hyperplasia (UDH) of the breast are morphological look-alikes, characterized by cellular streaming, solid growth, and a lack of high-grade nuclear atypia. Here, we report a challenging papillary lesion in the breast of a 48-year-old woman that presented with a double pitfall. A core needle biopsy showed a solid papillary proliferation of epithelial cells with oval to round overlapping nuclei, surrounded by a sclerotic stroma. This distorted lesion contained peripheral clefts and cellular streaming, without high-grade nuclear atypia. Immunohistochemistry showed diffuse heterogenous immunoreactivity for estrogen receptor and cytokeratin 5, and no immunoreactivity for chromogranin and synaptophysin. The immunohistochemical profile distinguished this sclerosed papilloma with extensive UDH from a solid papillary carcinoma. The lumpectomy specimen revealed a second challenge, where multiple epithelial islets without surrounding myoepithelial cells were observed near the papilloma, mimicking an invasive carcinoma. These islets displayed the same immunohistochemical profile as the sclerosed papilloma and they were surrounded by steatonecrosis and reactive fibroblasts, indicating epithelial displacement within the biopsy needle tract. A sclerosed papilloma with extensive UDH is a morphologically challenging mimic of a solid papillary carcinoma. Immunohistochemistry is helpful to distinguish both entities from one another. Extensive epithelial displacement in the biopsy tract made this case particularly challenging, as the displaced epithelial islets mimicked an invasive carcinoma. Pathologists should be aware of this uncommon double pitfall to prevent misdiagnosis.